Southside Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Southside vacation rentals

Interior

Cozy Nest Near The River

Cozy Nest Near The River
Woodland Heights
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment, seemed like it was brand new. Very clean, convenient location and host responds quickly to messages"
United States
Ken S.
$137 nightly
The price is $148
Jun 4 - Jun 5
Total with taxes and fees
Cozy Nest Near The River
Interior

Cozy Bon Air Guest Suite with Private Entrance

Cozy Bon Air Guest Suite with Private Entrance
Bon Air
$140 nightly
The price is $160
Jun 1 - Jun 2
Total with taxes and fees
Cozy Bon Air Guest Suite with Private Entrance
Exterior

The Enchanted Studio

The Enchanted Studio
Huguenot
$155 nightly
The price is $176
May 11 - May 12
Total with taxes and fees
The Enchanted Studio
Smart TV, fireplace, computer monitors

Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
10.0 out of 10, Exceptional, (8 reviews)
"It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family "
United States
Jessica H.
$280 nightly
The price is $323
May 8 - May 9
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
Exterior

Casa Terra: Pet-Friendly Eco Oasis with Gazebo

Casa Terra: Pet-Friendly Eco Oasis with Gazebo
Broad Rock
10.0 out of 10, Exceptional, (1 review)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
$317 nightly
The price is $362
May 12 - May 13
Total with taxes and fees
Casa Terra: Pet-Friendly Eco Oasis with Gazebo
Living area

Renovated Modern Stylish “Vibrant” 4bdrm Home

Renovated Modern Stylish “Vibrant” 4bdrm Home
Beaufont
9.4 out of 10, Exceptional, (8 reviews)
"The overall experience was nice. Everything was there as advertised, and we would definitely stay there again"
United States
Johnny W.
$735 nightly
The price is $840
May 11 - May 12
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home
Lobby

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (117 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
$188 nightly
The price is $215
May 11 - May 12
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Marina

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (233 reviews)
"Truly unique, perfectly appointed, cozy and warm with stunning views. A very special experience."
United States
Kristin K.
$188 nightly
The price is $215
May 10 - May 11
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Front of property

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Capt. Ron has a charming, welcoming, and delightful alternative to a standard hotel room on offer here. Super fun!"
United States
Robert
$256 nightly
The price is $292
May 23 - May 24
Total with taxes and fees
Cookie B
Beach nearby

Charming 2-bedroom home, with lake access, in the Richmond metro area.

Charming 2-bedroom home, with lake access, in the Richmond metro area.
Quinton
10.0 out of 10, Exceptional, (16 reviews)
"Great place. Peaceful. But close enough to the city to enjoy that too"
United States
Jeffery J.
$157 nightly
The price is $169
May 21 - May 22
Total with taxes and fees
Charming 2-bedroom home, with lake access, in the Richmond metro area.
House (1 Bedroom) | Interior

Hike, Golf & Explore! Peaceful Home in Montpelier

Hike, Golf & Explore! Peaceful Home in Montpelier
3.0 star property
Montpelier
$233 nightly
The price is $265
May 25 - May 26
Total with taxes and fees
Hike, Golf & Explore! Peaceful Home in Montpelier
1 bedroom, free WiFi, bed sheets

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
$139 nightly
The price is $160
May 11 - May 12
Total with taxes and fees
The Farmhouse Retreat
1 bedroom, in-room safe, free WiFi, bed sheets

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (23 reviews)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
$119 nightly
The price is $136
Jun 1 - Jun 2
Total with taxes and fees
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very Good, (17 reviews)
"Very nice home. "
United States
Shannon C.
$371 nightly
The price is $417
May 20 - May 21
Total with taxes and fees
Luxury Stay! 10 min away from Fort Lee.
Living area

The SageBrush Cottage

The SageBrush Cottage
North Highland Park
$280 nightly
The price is $320
May 10 - May 11
Total with taxes and fees
The SageBrush Cottage
Fridge, microwave, oven, stovetop

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (72 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
$160 nightly
The price is $183
May 13 - May 14
Total with taxes and fees
The Studio@ Eanes Drug
1 bedroom, desk, iron/ironing board, WiFi

Private Guest house with Parking and Wi-Fi in a Central Location

Private Guest house with Parking and Wi-Fi in a Central Location
Virginia Union
10.0 out of 10, Exceptional, (7 reviews)
"The place was very clean and easily accessible. The place is near I-64 and the railroad, but the noise wasn't enough to disturb our sleep. For us, the bed was very firm."
United States
Frank
$222 nightly
The price is $254
May 12 - May 13
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location
Terrace/patio

Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (5 reviews)
"Great spot to spend the evening while traveling through! Comfortable space.Host was very helpful through the check in process and my stay.Thanks Pamela!"
United States
Shawn P.
$174 nightly
The price is $200
May 14 - May 15
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
Fridge, microwave, oven, stovetop

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (64 reviews)
"Excellent accommodations!Great walkable location near local cafes & restaurants with a friendly neighborhood vibe."
United States
Patricia N.
$177 nightly
The price is $202
May 10 - May 11
Total with taxes and fees
Historic Haven in Church Hill
TV

Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (82 reviews)
"Easy check in and a pleasant quick stay "
United States
Megan M.
$335 nightly
The price is $358
May 11 - May 12
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southside Hotel Reviews

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

6/10 Okay
"There was no accommodation for disabled or handicapped visitors the toilet was very not even a toilet helper to help no handicapped rails in bathroom my sister had knee and hip surgery and I requested a handicapped room and breakfast was fair no fruit only green apples I will not be staying at this hotel again Hilton was next door same price I do visit short pump twice a year for shopping was planning a ladies fellowship next year will not be using this hotel"
Elizabeth 2-night trip
Posted 2 hours ago
Wingate by Wyndham Richmond Short Pump

Find out more about Southside

Everything you need to know about Southside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $183 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southside rentals

At Expedia, we put the best Southside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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